Urban principals can and should be at the center of creating school conditions that meet the needs of students and families in low-opportunity communities, not because they have all the answers or authority (they do not), but because they are in a conspicuous position to catalyze an authentic locally responsive learning process that can bring new possibilities and opportunities. A principal’s personal commitments, situational awareness, advocacy, critical reflection, and technical expertise can enable them to rethink and collaboratively reconstruct schools in ways that bring about social transformation. They can catalyze change by being sympathetic, compassionate, reflective, and hopeful individuals. They can serve as “tempered radicals” that learn with communities, and they certainly cannot wait any longer for a magic bullet reform or be afraid to make mistakes. To accentuate why I believe principals should be at the center of creating schools that can change the lives of their students, this chapter supplements previous chapters focused on alternative and social justice leadership approaches with cases that required principals to work with teachers, families, and communities to learn, reflect, and transform their schools. Each principal recognized the power of the status quo in their district, sought to improve the lives of students and families, succeeded in many areas, and struggled in others.